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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:07 UTC
NP-MRD IDNP0000458
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Hexanone
Description3-Hexanone, also known as 3-oxohexane or hexan-3-one, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. 3-Hexanone is a very hydrophobic molecule, practically insoluble in water and relatively neutral. 3-Hexanone is an ether and grape tasting compound. Outside of the human body, 3-Hexanone has been detected, but not quantified in, several different foods, such as pepper (capsicum), oregon yampahs, cinnamons, cloudberries, and cardamoms. 3-Hexanone, with regard to humans, has been found to be associated with several diseases such as nonalcoholic fatty liver disease, pervasive developmental disorder not otherwise specified, autism, and perillyl alcohol administration for cancer treatment. 3-Hexanone has also been linked to the inborn metabolic disorder celiac disease.
Structure
Thumb
Synonyms
ValueSource
3-OxohexaneChEBI
Ethyl N-propyl ketoneChEBI
Ethyl propyl ketoneChEBI
Hexan-3-oneChEBI
Chemical FormulaC6H12O
Average Mass100.1589 Da
Monoisotopic Mass100.08882 Da
IUPAC Namehexan-3-one
Traditional Name3-hexanone
CAS Registry Number589-38-8
SMILES
CCCC(=O)CC
InChI Identifier
InChI=1S/C6H12O/c1-3-5-6(7)4-2/h3-5H2,1-2H3
InChI KeyPFCHFHIRKBAQGU-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Cannabis sativaCannabisDB
      Not Available
Salvia rosmarinusFooDB
Zea mays L.FooDB
    • Carlos Macku, and Takayuki Shibamoto. Headspace volatile compounds formed from heated corn oil an...
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentKetones
Alternative Parents
Substituents
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-55.5 °CNot Available
Boiling Point123.00 to 124.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility14.7 mg/mLNot Available
LogP1.487 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility12.6 g/LALOGPS
logP10(1.59) g/LALOGPS
logP10(1.95) g/LChemAxon
logS10(-0.9) g/LALOGPS
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity30.05 m³·mol⁻¹ChemAxon
Polarizability12.2 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000753
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030904
KNApSAcK IDC00052141
Chemspider ID11025
KEGG Compound IDNot Available
BioCyc IDCPD-13223
BiGG IDNot Available
Wikipedia Link3-Hexanone
METLIN ID5721
PubChem Compound11509
PDB IDNot Available
ChEBI ID89891
Good Scents IDrw1005661
References
General References
  1. Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [PubMed:5556886 ]
  2. POWELL SG, NIELSEN AT: Condensation of butanal with 4-heptanone and 3-hexanone and attempted condensation of 2-ethyl-2-hexenal with 4-heptanone. J Am Chem Soc. 1948 Nov;70(11):3627-30. doi: 10.1021/ja01191a027. [PubMed:18102909 ]
  3. Johnson SD, Burgoyne PM, Harder LD, Dotterl S: Mammal pollinators lured by the scent of a parasitic plant. Proc Biol Sci. 2011 Aug 7;278(1716):2303-10. doi: 10.1098/rspb.2010.2175. Epub 2011 Jan 5. [PubMed:21208953 ]
  4. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
  5. Albright A, Gawley RE: Application of a C2-symmetric copper carbenoid in the enantioselective hydrosilylation of dialkyl and aryl-alkyl ketones. J Am Chem Soc. 2011 Dec 14;133(49):19680-3. doi: 10.1021/ja209187a. Epub 2011 Nov 16. [PubMed:22074559 ]